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CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!

Holiday home with private pool, near Duval Street

Photo gallery for CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!

Private home with Old Town Charm
Relax on the front porch swing
High ceilings and Dade County Pine
Queen bed, flat screen TV
Plush linens

Reviews

9.6 out of 10
Exceptional
4 bedrooms2+ bathroomsSleeps 10153.3 sq m

Popular amenities

  • Dryer
  • Washer
  • Kitchen
  • Pool
  • Barbecue grill
  • Outdoor space

Explore the area

View map
  • Place, Duval Street
  • Place, Southernmost Point
  • Place, Mallory Square
  • Airport, Key West, FL (EYW-Key West Intl.)

Rooms & beds

4 bedrooms (sleeps 10)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Queen Bed

Bedroom 4

1 Queen Bed

Other Space 1

1 Double Sofa Bed

2 bathrooms, 1 half bathroom

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Toilet · Shower only

Bathroom 3

Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Separate dining area
Garden

About this property

CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!

HISTORIC OLD-WORLD CHARM WITH MODERN AMENITIES AND A LAGOON-STYLE POOL....
Once you step through the threshold of this Old Town home you feel enveloped in vintage Key West.  Dade County wood surfaces, nautical accents plus appealing and comfortable decor make this a true "Captain's Quarters". Hang out in the living room with flat screen TV.
***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE

SLEEPING ARRANGEMENTS...
You will have many sleeping options while staying in this stunning home as it comfortably sleeps 8-10 guests. There are three bedrooms located in the main house and a one bedroom cottage off the rear deck by the pool.  As you enter the main hallway, there are two queen guest bedrooms immediately to your left and right. They each have TVs, storage for clothing and the option of using the hall or rear bathrooms. The master bedroom is fitted with a king size bed, flat screen, closet and has an interior door that leads to a full bathroom.  You will find a cast iron clawfoot tub with rain shower as well as a vintage pedestal sink. The rear bathroom off the family room has a tiled shower with glass door and a pedestal sink. There is a powder room off the kitchen that houses the washer and dryer. It has a door to the rear deck that can double for cottage use.  The cottage is your fourth bedroom with a queen size bed, pedestal sink, dresser and flat screen with a view of the pool!  If you have one or two more guests they can use the sleeper sofa in the family room. 

AMENITIES...
Captains' Quarters had updates completed in the spacious homes layout and decor in 2015. Impressively rich Dade County pine and high ceilings make this property a real stand out. The kitchen is fully equipped to meet your cooking needs and has a formal dining room steps away. Your family can dine together at the table for six or use the space to play games or cards.     

OUTDOOR LIVING...
Lush tropical landscaping greets you at the front gate and wraps around the property. Once inside, you will find a covered porch with a swing and seating area perfect for your morning coffee or to curl up with a book.  A winding path will take you around the side yard to a real gem; the lagoon-style pool!  The large private, heated pool is situated in the rear yard surrounded by a composite deck with plenty of seating. There is a gas grill and outdoor table covered with a large umbrella meant for six to dine al fresco and grill your fresh catch of the day.  If you are a sun worshiper you can kick back and relax on one of the five lounge chairs that surround the pool. Enjoy an outdoor shower to rinse off and head into town!

PARKING...
This home does not have designated parking but there is on street parking in the surrounding neighborhood.  Please refrain from parking in spots marked “residential permit”.

DISTANCES TO BEACHES...
Higgs Beach is 0.8 mi
South Beach is 0.9 mi
Smathers Beach is 1.7 mi
Fort Zachary Taylor Beach is 1.7 m

CONCIERGE SERVICES...
Enjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!

CANCELLATION...
Bookings canceled at least 30 days before the start of stay will receive a 100% refund. Bookings canceled at least 14 days before the start of stay will receive a 50% refund.

ISLAND TIME AWAITS...

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Amenities

Pool
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
Property Registration Number 25230-28078

About the area

Key West

Located by the sea, this holiday home is in Old Town Key West, a neighbourhood in Key West. Ernest Hemingway Home and Museum and Southernmost Point are notable landmarks, and the area's natural beauty can be seen at Fort Zachary Taylor Historic State Park and Florida Keys Beaches. The Kite House and Key West Butterfly and Nature Conservatory are also worth visiting. Discover the area's water adventures with jet skiing and scuba diving nearby, or enjoy the great outdoors with ecotours and cycling.
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Map
Key West, FL

What's nearby

  • Duval Street - 12 min walk - 1.1 km
  • Southernmost Point - 14 min walk - 1.2 km
  • Ernest Hemingway Home and Museum - 15 min walk - 1.3 km
  • Smathers Beach - 4 min drive - 2.0 km
  • Mallory Square - 5 min drive - 2.4 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 10 min drive

Restaurants

  • ‪Sandy's Café - ‬1 min walk
  • ‪El Siboney Restaurant - ‬6 min walk
  • ‪Dions Truman & White - ‬2 min walk
  • ‪Dairy Queen - ‬5 min walk
  • ‪Mangia Mangia - ‬11 min walk

Frequently asked questions

Does CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!! have a pool?

Yes, this property has a pool. Pool types include heated pools.

Is CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!! pet-friendly?

No, pets are not allowed at this property.

What time is check-in at CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!?

Check-in begins at 4:00 PM.

What time is check-out at CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!?

Checkout is at 10:00 AM.

Where is CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!! located?

Located in Old Town Key West, this holiday home is within a 15-minute walk of Key West Firehouse Museum, Duval Street and Florida Keys Beaches. Ernest Hemingway Home and Museum and Southernmost Point are also within 1 mile (2 km).

Reviews

9.6

Exceptional

9.8/10

Cleanliness

9.8/10

Check-in

9.8/10

Communication

9.6/10

Location

9.8/10

Listing accuracy
Rating 10 - Excellent. 160 out of 192 reviews
Rating 8 - Good. 23 out of 192 reviews
Rating 6 - Okay. 7 out of 192 reviews
Rating 4 - Poor. 0 out of 192 reviews
Rating 2 - Terrible. 2 out of 192 reviews

Reviews

10/10 Excellent

Devotion808 g.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect stay, awesome communication with the property manager at all times 5
Stayed 3 nights in Aug 2025

10/10 Excellent

Britt N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place!

We loved this house. It was nice to be a little off the beaten path but a short walk/bike ride everywhere. Great pool, comfortable beds, well stocked kitchen (plates, utensils, cookware, some spices) and plenty of room for 6 adults.
Stayed 4 nights in Jul 2025

10/10 Excellent

Christine P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing stay!

We loved the house. From the location, to ambiance and heated pool- it was all amazing! We didn’t cook at all and spent most of our time out and about, but we used the pool day and night. We had 2 couples and 2 additional friends and it was the perfect amount of space and privacy! Would highly recommend this spot and nearby is a cute little bike shop to easily rent a bike cruiser or golf cart for your time!
Stayed 2 nights in Apr 2025

10/10 Excellent

Donna W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Captain's Quarters

The location and condition of the property, ease of check-in, communication with the property representatives, and entire vacation experience with friends were unforgettable.
Stayed 4 nights in Jun 2024

10/10 Excellent

Shawna G., Glendale

Liked: Cleanliness, check-in, communication, location, listing accuracy

Such a great place!

Had such a great time! Perfect location. Easy access. Best family vacation spot!
Stayed 3 nights in Aug 2019

10/10 Excellent

Irina S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Vacation with family friends

Stayed for a week and had a great time. Lovely house, amazing pool, great location. Highly recommend.
Stayed 6 nights in Apr 2021

10/10 Excellent

Brenda A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great time

Great place, did echo lots but not a real bother. Great location and close to good food and needs in walking distance!
Stayed 5 nights in Nov 2023

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nice property and manager

amazing property and communication with the manager.
Stayed 3 nights in Jul 2023

10/10 Excellent

Kaylee F., United States

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great house with a great location

Very spacious house for a large group, with a nice size pool. Easy check in and check out. They accommodated early check in and out. Quiet neighborhood with plenty of places to walk to and not far from duval!
Stayed 5 nights in Jul 2023

10/10 Excellent

Beach Houses D., New Albany, OH

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Bacstion

Wonderful house and an amazing pool! Would highly recommend!
Stayed 5 nights in Jun 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

JOHN T.

Perfect Place

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Excellent as described!

10/10 Excellent

Crissie B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Our Favorite Stay!

We’ve stayed at this property multiple times and it’s always a favorite of ours! The pool is full sized & heated, which is rare in Key West! The property manager is always great with communication. Our pools heat went out at the end of our stay, but Wendy was on it to get people there to get it fixed. Definitely recommend staying here!
Stayed 7 nights in Jan 2023

10/10 Excellent

Sandra S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great property in a great location!

We had a wonderful time in this comfortable, perfectly decorated pool home. Everything was made easy for us from check in to check out, and we had no problems getting to all the fun spots to visit in Key West. The pool is definitely a plus when traveling in the time of Covid and when the weather is a touch too windy to be out on a boat. Look for this property if you want a great place to relax with plenty of room for a family or group of friends.
Stayed 4 nights in Feb 2021

10/10 Excellent

Lori D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Place!

This place was everything it said it would be and did not disappoint our group! It is such a cute place to stay with only 4 blocks from Duvall street. Although we were within walking distance to Duvall, we did rent a golf cart for other excursions. We will definitely keep this place in mind again for our next visit. The property Manager, Melanie, was great getting us in early to the house.
Stayed 4 nights in Sep 2022
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Tania G.

Celebration of life

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We got together as a family to celebrate my father-in-law‘s life. A third generation conch that has lived his life in Key West. Captain’s Quarters was perfect.
Stayed 2 nights in Apr 2024

10/10 Excellent

Dan L., Chicago, IL, USA

Liked: Cleanliness, check-in, communication, location, listing accuracy

Chill Key West Location w/Pool

Very nice house with pool in Key West. 3 in-house bedrooms with 2.5 baths. The 4th bedroom is a pool-house with sink. Very cozy and clean overall. Would recommend to others. Property manager and overall communications were great. Parking wasn't a huge problem. It is a 20-30 min walk to Duval Street activities, so if you aren't renting a bike or golf cart, an Uber would be recommended on the steamy nights after the bars.
Stayed 5 nights in Jun 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Jessica J.

We Can't Wait Till Next Year

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: A group of 6 adults have been traveling to Key West for the past 5 years. This is the best house we have stayed! All the rooms are large and everything in on one level. The best part is the pool. It is hard to find a full size pool and ample pool deck space and this house has both! We hope to stay again next year!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Rosemary D., Bristol, NH

Key West Christmas!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We rented this house for the week before Christmas rather than giving gifts. It was a wonderful opportunity to spend time together with family. The house was perfect for our family. We didn’t need a car and walked out biked everywhere. The weather wasn’t fabulous but we still had a great time. The pool area was great, the kitchen well supplied, and the front porch was a great place for our grandchildren to hang ou with neighborhood cats!
Stayed 7 nights in Dec 2019

10/10 Excellent

Linda C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect for our family celebration

We had 3 adults varying ages celebrating a 30th birthday. The house couldn't have been more perfect. Charm alongside the perfect layout for personal space as well as areas to be together at the pool family room or dining room. The pool amazing. House immaculate with all amenities needed. Bikes to rent are just a couple blocks away (walking) we had no issue parking for one car. Easy bike ride or nice walk to Duvall. And our host Melanie was a star! Quick to respond but really everything was laid out clearly from start to finish, there wasn't much to ask other than what kind of coffee maker was available (both drip and keurig btw which was great) We would love to stay at this property again. Easy. Beautiful. Thanks Melanie!
Stayed 4 nights in May 2024

10/10 Excellent

Amy T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Hidden Gem

This home is amazing. House was exactly as described. We could walk everywhere, plenty of places to eat and shop within one mile. Having the pool was definitely a plus and had free entertainment from the large Iguanas that would stroll along the top of the fence in back yard (no worries the are harmless). We all agreed we would rent again. Our property manager, Melanie, was a delight to deal with. We had a slight issue and it was handled in under an hour. She checked in us a few times in case we needed anything. It was nice knowing the Melanie was there for us if we had questions or concerns, or just simply needed some tourist advice. We enjoyed our stay very much!
Stayed 4 nights in Jun 2022

10/10 Excellent

S C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Must Stay Location!

The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We spent 4 days and 3 nights. Captains Quarters was wonderful. Great location with avg transportation cost of 8. Loved the front porch and the neighborhood. Keep in mind there is an early noise ordinances at 8pm so you need to be mindful at the pool if night swimming. Woke up with the chickens every morning and relaxed in this home. The bathtub is high and for older folk would be difficult but there are two other showers one outdoors which was great under the stars! The beds and pillows were top notch and we all slept very well. Biggest issue was the deck door to the pool was very difficult to open. It stuck a lot. Thank you to the host for the great communication and I highly recommend using their free concierge service. We had food waiting for us after a very stressful travel day. They really aided in our decompression. I will be back and will stay here again.
Stayed 3 nights in Jan 2025

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

Mini Paradise

This property is a family-sized private oasis in the middle of fabulous and crazy Key West. The house is exactly what you see in the photos. Modern island living with perfect design, space and every convenience. We spent our week grilling and swimming at the delightful pool. We even had to force ourselves out to the outrageous sailboat charter we'd arranged because time stood still and we had a hard time leaving the property. We have all spent the week since we arrived home wishing we'd booked another week away! Every bedroom is fully stocked with linens and a TV. The kitchen boasts every appliance you may need and the separate dining room is a great place to play games and gossip while planning for the next day (which will invariably be hanging in the pool),. THIS is a vacation destination! THANK YOU SO MUCH!
Stayed 5 nights in Aug 2021
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Joyelle L.

Great!

Rating Details: The property manager was more than helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Everything was great, smooth, and everyone enjoyed. Easy process from start to finish. I received a text prior to arrival from the property manager. I never received a reply back when I texted on Sunday, asking if a 2 hour later check out could be granted, absolutely understanding if it could not. I never heard back, which was a little frustrating, and the reason I gave 4 stars for professionalism. Even a simple No would have been fine with me. We thought the house was great, bigger than it appeared online, pleasantly surprised. It was just on the edge of comfortability to walk to Duval street. Some of us were OK, some of us opted to Uber, which was 10-15 each way. The outside room, it had a strong musty odor (we still used, just want to warn those with allergies, they would be definitely impacted). Also, roosters start at about 1:30am, making it almost impossible to sleep in certain areas. Part of the fun though. But a light sleeper may not be so happy. We loved it, really no complaints, just mentioning things that others may be sensitive to.
Stayed 4 nights in Aug 2019

2/10 Terrible

Ashley R.

Disliked: Cleanliness, communication, listing accuracy

DON’T DO IT

The rental management company ruined our stay and it’s just standard practice. During our stay, the separate cottage bedroom was not usable because it was infested with huge ants. Literally, ANTS WERE EVERYWHERE. The cottage accounts for a separate bedroom by the pool, connected to the outdoor shower. They knew about ants before we arrived but waited until we got there so we could let the exterminator in with the key. So they finally spray toxic chemicals all over the bedroom and tell us we shouldn’t go in for 48 hours. So…we don’t have enough bedrooms. Dead ants covered the bedroom. Next, you’ll be interrupted by the pool cleaners who demand you leave the pool area for 2 hours, followed by the landscapers who came AFTER the pool was cleaned and spent 3 hours cutting, mowing, trimming bushes, and then blowing all the debris (back into the pool) I contacted management who was “out for the day” and she never called me back. I complained about not getting a call back and this woman actually created a fake screen shot of her fake attempt at trying to call me….or someone programmed in her phone as “tenant blah blah blah” she claimed she tried to call back and the call was “cancelled” so she is just dumb. She called a number, pressed cancel, and then took a screen shot and this was her proof of trying to contact me. I own property and would fire my team if they acted this way. Don’t rent from this company.
Stayed 6 nights in May 2024

10/10 Excellent

Riley N.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay, enjoyed our time. The pool is bigger than the pictures give it credit for!
Stayed 3 nights in Jul 2025

About the host

Hosted by Wendy Zintsmaster & Team

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Languages:

English

Premier Host

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